Naphthalene polycarboxylic acid arylides and a process for preparing the same



Patented Aug. 3, 193? UNITED ST-TS ATE'E' OFFIQE NAPHTHALENE POLYCARBOXYLIC ACID' ARYLKDES AND A PROCESS FOR PREPAR- ING THE SAME Max Wyier and Arnold Kershaw, Blackley, Manchester, England, assignors to Imperial Chemical Industries Limited, a corporation of Great Britain No Drawing. Application June 25, 1935, Serial No. 28,373. In Great Britain July 5, 1934 Claims.

In co-pending U. S. application Serial No. 454 filed January 4, 1935, there is described the manufacture of new acenaphthene-5- and 5:6- biscarboxyalkylanilides in which alkyl is prefer- 5 ably methyl or ethyl and the anilide residue may carry a methyl or chloro substituent.

This invention relates to the preparation of new l,8-dicarboxynaphthalene-4-carboxyalkylanilides or 4,5-biscarboxyalkylanilides which are obtainable by dichromate oxidation in acid solu- Example 1 To a boiling solution of 135 parts of acenaph thene-5-carboxyethylani1ide in 1500 parts of 30 glacial acetic acid are added 300 parts of sodium dichromate in portions during 2 hours, then a further 75 parts during 1% hours. After boiling for a further half hour, the mixture is poured into 5000 parts of water, the resulting precipitate is filtered off, washed free from chromium salts, and purified by dissolving in sodium carbonate solution, filtering and reprecipitating with mineral acid. When dry it forms a yellow crystalline powder, which crystallizes from glacial 40 acetic acid in pale yellow plates. It appears to be the anhydride; analysis N (found) 4.1%, N (calc. for anhydride) 4.06%.

Example 2 To a boiling solution of 33.6 parts of acenaphas described in Example '1. It crystallizes from ethyl alcohol in light yellow prisms of M. P.

206 C., and appears to be the anhydride; analysis,

N (found) 5.7%, N (calc. for anhydride) 5.69%.

We claim: 5 l. The process for preparing new 1,8-dicarboxynaphthalene-carboxyalkylanilides w hi 0 h comprises subjecting to a chromic acid oxidation 2. compound of the formula 10 HO-(JH wherein one X stands for the group in which R stands for an alkyl radical and Ar stands for an aryl radical, and the other X stands for the same group or for hydrogen.

2. The process for preparing new 1,8-dicarboxynaphthalene carboxyalkylanilides which comprises subjecting to a chromic acid oxidation 9' in an acetic acid medium a compound of the formula-- i H(|3-GH l x x wherein one X stands for the group /R -ON in which R stands for an alkyl radical and Ar stands for an aryl radical, and the other X stands for the same groupor for hydrogen.

3. A 1,8-dicarboxylic acid compound of naphtha1ene-4,5-biscarboxya1ky1anilide which is idenwith the compound obtainable by chromic acid tical with the compound obtainable by chromic oxidation of acenaphthene-5-carboxya1ky1ani1ide.

acid oxidation of acenaphthene-5,6-biscarboxy- 5. Compounds identical with those obtainable alkylanilide. by the process of claim 2.

4. A 1,8-dicarboxy1ic acid compound of naph- MAX WYLER.

tha1ene-4-carboxya1ky1ani1ide which is identical ARNOLD KERSHAW. 

